Most people do all they can to stay out of the courtroom, but President Donald Trump does the opposite. Over the decades, Trump has used the legal system to get what he wants. But that doesn’t mean things always turn out in his favor. Trump has been involved in “3,500 legal actions in federal and state courts during the past three decades. They range from skirmishes with casino patrons to million-dollar real estate suits to personal defamation lawsuits.”
You can browse the federal court system database, as well as online portals for the New York and Florida court systems if you’re so inclined. And this doesn’t even count the suits levied against Trump since he became president. There’s simply too much to look through, so we reviewed the biggest, most public lawsuits and found 15 that were particularly interesting.
1. Trump University
- What happened: An attempted higher education scheme leads to inquiries for illegal business practices.
We’ll start our list with the most recent and noteworthy, excluding the cases brought against Trump as president. Trump University (actually a seminar) charged roughly $1,500 to $35,000 to students who wanted to learn Trump’s real estate secrets. Students alleged that the seminar used high-pressure, deceptive sales tactics to push them into real estate and business programs.
The settlement involving Trump University ended up costing Trump $25 million, but perhaps the most damage was to his reputation. Billing himself as a successful businessman during his campaign for president, the Trump University fiasco reeked of snake oil.
Next: A government sting leads to legal troubles.
2. Fair Housing Act violations
- What happened: Trump was accused of racial discrimination.
In 1973, renters in a Brooklyn apartment complex accused Trump of racial bias. His company managed the 39-building complex, and after the government set up a “sting” of sorts, it sued the company. Trump fired back, filing a countersuit for $100 million, which the court threw out. The suit settled in 1975 out of court, and Trump never admitted guilt.
The impact? The series of events was a precursor to accusations of racism and nationalism that followed Trump all the way to the White House.
Next: Trump gets lucky as he settles a $2 million lawsuit.
3. Trump’s Taj Mahal defamation suit
- What happened: Trump tried to dismiss someone for disagreeing with him.
In 1990, when a business analyst predicted Trump’s Taj Mahal casino in Atlantic City would fail, Trump pushed to have the man, Marvin B. Roffman, dismissed. Roffman sued Trump for $2 million for defamation and eventually settled for $750,000. The lesson here? Trump doesn’t like disloyalty. He’ll go after you if you don’t toe the line.
Next: Casino chips become an illegal loan.
4. Daddy’s cash infusion
- What happened: Fred Trump gave Donald an illegal loan.
In another highly suspect move given Trump’s “successful businessman” persona, Donald Trump’s father Fred Trump gave one of his son’s hurting casinos a cash infusion. Basically, Fred bought roughly $3.5 million in chips at the Castle Casino in Atlantic City and never cashed them out — a stealthy way to inject cash into the business. To regulators, this amounted to an illegal loan. As a result, the casino received a $65,000 fine.
Next: Trump faces a $125 million sexual harassment suit.
5. Jill Harth sexual harassment suit
- What happened: Trump was accused of sexual assault.
We all know about Trump’s “grab ’em by the p***y” moment. But his checkered history with sexual harassment goes way back. In 1997, makeup artist Jill Harth sued him for $125 million after she claimed he groped her, among other things, a few years prior. She recounted the alleged assaults to The Guardian, though she eventually settled for an undisclosed amount.
Next: Divorces are expensive. Really expensive.
6. Divorce from Ivana
- What happened: Trump’s expensive divorce revealed his financial troubles.
Trump’s been married three times. His first marriage to Ivana Trump ended in one of the world’s most expensive divorces — around $25 million. Why is this interesting? Consider this New York Times article from 1991:
Mrs. Trump and her lawyers said she was entitled to half of Mr. Trump’s assets, which they then valued at around $5 billion. But the erstwhile billionaire apparently never had that much to begin with and certainly does not have it now. Mr. Trump’s financial problems brought him near bankruptcy last year and forced him to ask his banks to rescue him by lending him more money to pay off bills.
Next: When billionaires don’t play nice with each other
7. The Steve Wynn affair
- What happened: Trump was accused of spying and conspiracy.
A rampant issue in Trump’s White House? Palace intrigue. From tapes to wiretaps, there’s no shortage of drama coming out of the West Wing these days. We had a glimpse of this intrigue back in the late ’90s when Trump endured a long legal battle — involving suits, countersuits, and allegations of spying and conspiracy — with Steve Wynn, a rival casino owner in Atlantic City.
But Trump and Wynn magically settled on the exact same day and time they were supposed to air it all out in court. It’s a fishy tale with many twists and turns. Interestingly enough, Wynn eventually took over the Republican Party’s fundraising in February 2017.
Next: A $139 million fraud
8. The Bayrock Group fiasco
- What happened: Trump defaulted on a loan, and made some Russian connections.
In the early 2000s, a Trump International Hotel & Tower was supposed to be built in Fort Lauderdale, Florida, but it never happened. Well, the tower was built but not as planned. Trump, who partnered with development company Bayrock Group, defaulted on his $139 million loan needed to build it. Investors sued for fraud, and Trump eventually disentangled himself from the project. In partially built condition, the hotel was eventually sold and opened as Conrad Fort Lauderdale Beach.
The real story involves apparent Russian connections Trump had. Some Bayrock execs had worked for the Soviet government, and their office — located in Trump Tower — served as a meeting place between Trump and many Russian contacts. All of this is still being worked out, of course. But considering the concerns about Russia these days, this case shows how the story dates back.
Next: Who knew the American flag could cause so much trouble?
9. The flag at Mar-a-Lago
- What happened: Trump made a lawsuit against Palm Beach, citing free speech.
A relatively small fine over a flag doesn’t seem like a big deal. But Trump’s response to fines from the city of Palm Beach — levied to his Mar-a-Lago Resort in 2006 — showcased one of his trademark tendencies: to counterpunch with everything he has. Palm Beach fined Trump for an oversized American flag, and he swung back with a $25 million lawsuit for infringing on his right to free speech. The two parties eventually settled.
Next: Trump responds to a $40 million lawsuit with a $3 billion countersuit.
10. A run-in with Deutsche Bank
- What happened: Trump failed to pay a loan and was sued by Deutsche Bank.
Few people in real estate escaped the 2008 housing market collapse unscathed. During that time, Deutsche Bank sued Trump for $40 million regarding a $640 million loan he took out to build the Trump International Hotel and Tower in Chicago. But, as we know, Trump likes to counterpunch. So he did — in the form of a $3 billion countersuit claiming his reputation was damaged. The two parties eventually settled, with the loan being extended. Count this as another notch in the “great dealmaker’s” belt.
Next: Trump lashes out at a law firm for using his name on its website.
11. Trump vs. Morrison Cohen
- What happened: Trump allegedly failed to pay for legal services.
Trump doesn’t like people taking shots at his reputation. And the law firm Morrison Cohen (previously hired by Trump) learned the hard way. Trump filed a $5 million suit against the firm for merely mentioning his name and linking to news articles on a website. They countersued and the suit was eventually dismissed.
Why did Morrison Cohen include anything about Trump on its site? He allegedly didn’t pay them for their services. Reports say he owed around $500,000 in legal fees. His evident unwillingness to pay those who work for him is another part of the Trump mystique that followed him to the White House.
Next: A canceled project makes investors feel tricked.
12. Trump Ocean Resort Baja Mexico
- What happened: Trump kept investor money after a project failed.
“The next Cabo” — sounds like a good investment, right? A lot of people thought so, which drove investors to make deposits on condos to be built as part of Trump Ocean Resort Baja Mexico. Unfortunately, the project was eventually canceled. The investors sued Trump after he told them he couldn’t return all $32.2 million of their deposits. He also claimed he shouldn’t be held responsible for the project’s collapse, as he was merely its spokesman. Again, he settled with the investors for an undisclosed amount in 2015.
Next: Trump’s rocky relationship with the media leads to a huge lawsuit.
13. Trump vs. Univision
- What happened: Trump sued Univision for not airing Miss USA, after he made disparaging remarks about Mexican immigrants.
Trump has had a contentious relationship with the media since venturing into politics. But there were indications the relationship would sour even as he starred in his hit TV show. Trump sued Univision in 2015 for $500 million when the network canceled its airing of the Miss USA pageant after Trump’s infamous remarks about Mexican immigrants. He eventually settled out of court.
Next: A $5 billion defamation lawsuit
14. TrumpNation controversy
- What happened: Trump’s ego was bruised after a book claimed he wasn’t worth billions.
A shot at Trump’s reputation sparked a lawsuit against Timothy O’Brien, author of TrumpNation: The Art of Being the Donald. In the 2015 book, O’Brien says Trump’s net worth is between $150 million and $250 million, despite Trump telling the author he was worth billions. Trump filed a $5 billion lawsuit against O’Brien, claiming damage to his reputation. A judge tossed it, saying the author was not trying to defame him.
Trump took this as proof he is a billionaire. “That’s what it is; it’s indisputable,” Trump said, per a report from ABC News. “If it wasn’t, I wouldn’t have brought the lawsuit.” This wasn’t the last time Trump claimed “total and complete vindication” after an otherwise damaging event.
Next: Further proof that Trump can’t take a joke.
15. Trump vs. Bill Maher
- What happened: Trump sued Bill Maher for making a joke.
Finally, the cherry on top. Trump has been criticized for being thin-skinned — a contrast to his “alpha” businessman persona. But nothing backs up this notion more than his lawsuit against comedian Bill Maher. Trump sued Maher after Maher made a joke about Trump’s mother having sex with an orangutan (the result: Trump himself). The $5 million suit was eventually withdrawn.
It was a gross and inappropriate joke, but a joke nonetheless. And if you want to be president, the ability to roll with the punches is pretty important.